The preparation of α-substituted, β-hydroxy piperidines and pyrrolidines: The total synthesis of febrifugine

Tetrahedron Letters

Volumn 37, Issue 19, 1996, Pages 3255-3258

  Burgess, Laurence E ^a,b   Gross, Elizabeth K M ^a   Jurka, Joe ^a  

^a PFIZER INC   (United States)

^b AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANTIMALARIAL AGENT; FEBRIFUGINE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029880759     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00527-8     Document Type: Article

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21. Depending on the dry ness of the epoxidation solvent, compound 6 was isolated in the non-hydrated and hydrated form: Formula Represented
22. 3: 171.0892; Found: 171.0904.
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28. 5: 373.1638; found: 373.1646
29. Acidic conditions resulted in significant amounts of dehydrated material. For a similar deprotection see Wenkert, E.; Hudlicky, T.; Showalter, H. D. H. J. Am. Chem. Soc. 1978, 100, 4893.
30. From this deprotection reaction, diastereomer 1 (10) provided a solid which had spectral properties characteristic of the natural product.